CHAPTER 1 Learning Activities 1

Worksheet 1 This worksheet is about identifying the special nature of the benzene hydrocarbon. Complete this graphic organiser of ideas: 1. 2. 3.

Similarities

BENZENE

CYCLOHEXENE

Differences With regards to 1. 2. 3. 4. Worksheet 2

The bond length between carbon-carbon bonds in benzene is greater than a single carbon-carbon or double carbon-carbon bond.

This worksheet is all about the bonding in benzene.

The bond angle between the carbon atoms in a benzene ring is 90o Each carbon atom in a benzene ring has four molecular orbitals. Colin Bonds between carbon and hydrogen atoms in benzene are molecular bonds.

Ann

Yanlan Shaun Overlap of s and p orbitals create the bonds in a benzene molecule. Benzene is an unsaturated molecule and therefore prefers to undergo addition reactions rather than substitution reactions. Mary

Dave The benzene molecule is a perfect hexagon shape and is more stable than expected.

Above and below the carbon ring are orbitals for the delocalised electrons.

Wenli

Imran

Only TWO of these statements are completely correct. Which are these? Correct the other six statements by altering a key word. Worksheet 3

This worksheet is about electrophilic substitutions reactions of benzene.

1. Consider the bromination of benzene. (a) Complete the overall equation for bromination. C6H6 + Br2 + ..

(b) What is the halogen carrier in this reaction? (c) (i) What is the electrophile in this particular reaction? (ii) Why does this electrophile attack the benzene ring?

(d) Show the mechanism of this reaction with the help of curly arrows.

2. Consider the nitration of benzene. (a) Complete this equation for the formation of the electrophile. HNO3 + 2H2SO4 + .. + .

(b) Draw the structure of di-substituted and tri-substituted products from the nitration of benzene.

3.

Consider the alkylation of benzene by the Friedal-Craft reaction. (a) Complete the overall equation. C6H6 (b) + C2H5Cl .. +

(i) What is the catalyst in this substitution? (ii) What is the electrophile? (iii) Write an equation to show the formation of this electrophile.

Worksheet 4

This worksheet aims at testing your knowledge about nomenclature and structural formula of arenes and substituted phenols. Match the correct name to the correct formula by drawing a line between the two.

Name

Structural Formula

COOH 4-nitrophenol OH

phenylmethanol

OH OH NO2

2-chlorophenol

OH CH3 3-hydroxybenzoic acid Cl Cl benzene-1,2-diol OH

CH2OH

2-chloro-methylbenzene Worksheet 5 This worksheet aims at testing your knowledge of the important chemical reactions of phenol.

Give the structural formula(e) and name(s) of the organic product(s) formed by the following reactions.

Structural Formula

Name

Na or NaOH

CH3Cl AlCl3

OH dilute HNO3

Br2

N= N

Worksheet 6 This worksheet aims at comparing aromatic alcohols with aliphatic alcohols. Complete the table to show the comparison.

Comparison

Phenol (Aromatic)

Ethanol (Aliphatic) neutral

1.

pH

2.

Reaction with neutral iron (III) chloride solution no reaction

no reaction

3. Oxidation with acidified potassium dichromate (VI) 4. Reaction with dilute sodium hydroxide solution

no reaction

5. Reaction with sodium metal

few bubbles of hydrogen gas

6. Reaction with sodium hydrogen carbonate 7. Reaction with bromine in dark

no reaction

no reaction

8. Reaction with carboxylic acid

no reaction

Worksheet 7 Try this spiral crossword as a fun way of consolidating knowledge about phenols. Answer each of the following clues by starting in the square marked 1 at the centre of the grid and writing your answer in a clockwise spiral. The last letter of each answer is the first letter of the next. Follow the direction shown by the arrows and do not let any word cross the bold lines. To help the number of letters for each answer is given in brackets.

1. The colour neutral iron (III) chloride goes when phenol is added. (6) 2. The number of different elements in a phenol molecule. (5) 3. The reaction of phenol with an acid chloride is an example of this type of chemical reaction. (14) 4. The phenoxide ion is an example of this type of organic species. (11) 5. This type of substitution takes place on the benzene ring with phenol and bromine. 6. An old chemical name for phenol. 7. This element is responsible for phenol burning with a sooty flame. (6) 8. This phenol derivative is formed when phenol is reacted with dilute nitric acid. (11) 9. This indicator can be used to show the acidic nature of phenol. (6) 10. Physical state of phenol at room temperature. (5) 11. Describes how the negative charge of the phenoxide ion is stabilised by the benzene ring. (14) 12. The name of the catalyst used when adding hydrogen to the benzene ring of phenol. (6) 13. At 41C phenol changes to this. (6)

CHAPTER 2 Learning Activities 2

Worksheet 1 This worksheet is all about carbonyl compounds. (A) CH3-CH2-CHO (B) H-CHO (C) CH3-CH2-CO-CH2-CH3

(D) CH3-CH2-CH2-COOH

(E)

CH3-CO-CH3

(F)

C6H5-CHO

1. Name all of these carbonyl compounds. 2. Which two are structural isomers? 3. Which ones would produce a silver mirror with Tollens reagent? 4. Which would not produce a precipitate with 2,4-dinitro-phenylhydrazine (Bradys reagent)? 5. Which would fizz when added to a carbonate? 6. Which would burn with the sootiest flame? 7. Which is an aromatic compound? 8. Which would be reduced to (i) propan-1-ol ? (iii) benzyl alcohol? 9. Which would be oxidised to (i) propanoic acid? (iii) methanoic acid? 10. Give the mechanism for the nucleophilic addition reaction of hydrogen cyanide to compound A. (ii) benzoic acid? (ii) propan-2-ol? (iv) methanol?

Worksheet 2 This worksheet is all about oxidation and reduction of carbonyl compounds. Complete the table below by drawing the structure and naming the organic product from reduction or oxidation of the named carbonyl compound. If there is no reaction then say so. Oxidation Structure Name Name Reduction Structure

propanal

butan-2-one

methanal

propanone

pentan-3-one

ethanal

CHAPTER 3 Learning Activities 3

Worksheet 1 This worksheet is to improve your IT skills. The table shows the boiling points of the first six carboxylic acids in the homologous series with a general formula CnH2n+1COOH.

value of n 1 2 3 4 5 6

name of carboxylic acid methanoic ethanoic propanoic butanoic pentanoic hexanoic

boiling point o /C 101 118 141 164 186

molecular formula

relative molecular mass

1. Complete the table by calculating the relative molecular mass of the carboxylic acid [Ar(C) = 12, Ar (H) = 1, Ar (O) = 16]

2. Using a spreadsheet program arrange your data as shown below:

A 1 2 101

B 118

C D relative molecular mass 141 164

E 186

3. Using the chart options draw a line graph of boiling point (y-axis) against relative molecular mass (x-axis). Label it Boiling Point Graph. Preview the chart before you print it. Try other types of charts and choose the most effective one. 4. Use your graph to predict the boiling point of hexanoic acid.

Worksheet 2 This worksheet is all about the formation of esters. Compete the table by naming the ester and/or identifying the original alcohol and carboxylic acid it was made from.

Ester

Alcohol

Carboxylic Acid

CH3COOC2H5 name

CH3OH

C2H5COOH

HCOOC3H7 .name

C4H9OH

CH3CH2CH2COOH

C3H7COOC3H7 .name..

Worksheet 3 This multiple choice worksheet is to test your knowledge of carboxylic acids. Select either A, B, C or D. Only one of the answers is completely correct. 1. Which one of the following substances would be oxidised to 2-methylpropanoic acid? A. (CH3)2CHCH2OH C. CH3CH2CH2CH2OH B. CH3CH2CHOHCH3 D. (CH3)3COH

2. Which is the best description of the reaction between C3H7OH and HCOOH? A. addition C. esterification B. hydrolysis D. elimination

3.

When phenylethanoate is hydrolysed by excess aqueous sodium hydroxide, the products of the reaction are A. phenol and ethanoic acid C. ethanol and benzoic acid B. phenoxide ions and ethanoate ions D. phenol and ethanoate ions

4.

Which of these organic compounds would bubble when magnesium is added? A. C. CH3CHO CH3COCH3 B. D. HCOOH HCHO

5.

Which one of the following compounds would react with the product of its own oxidation product to form a sweet smelling liquid? A. C. propanal propan-1-ol B. propanone D. propan-2-ol

6.

Which of these acids is the strongest? A. C. CH3COOH Cl2CHCOOH B. D. ClCH2COOH Cl3CCOOH

Questions 7 to 12 refer to the four carboxylic acids A, B, C and D listed below. A. ethanoic acid B. ethanedioic acid C. butanoic acid D. benzoic acid 7. Which of these acids is least soluble in cold water? 8. Which of these acids will decolourise a warm acidified solution of potassium manganate (VII)? 9. Which of these acids has the lowest boiling point? 10. Which acid can form two sodium salts? 11. Which of these acids is found in rhubarb and is called oxalic acid? 12. Which of these acids when concentrated is called glacial as in cold weather it crystallises?